Your dark and mysterious payroll past comes back into your life. Another notice. Something unreadable. You thought you'd left this all behind. But here it is again. Your pulse quickens. You're back under the tax agency's smoldering gaze. And this time, they won't take no for an answer.

Hey, Tyler. I noticed you have seven dependents on your tax form. Usually those would be people in your immediate family who share your living expenses and rely on your income, like a spouse and kids. Are you sure that all of these people would actually be considered dependents for tax purposes?

Deel is like if a pickup artist did payroll. Deel is the stereotypical tech-bro, “move fast and break (your) things,” the-rules-are-for-thee-and-not-for-me, all-glitz-no-substance disappointment. It looks pretty in the demo, even if those fancy buttons and cool apps never work as expected. 

When you work overtime, you’re paid time and a half. The OBBBA only applies to the “and a half” portion of your pay. The OBBBA only applies to federal overtime, or hours worked beyond 40 hours in a week.

Many companies with fewer than 200 people will literally sign away legal control of their employees and pay multiple times more for payroll services.  Just so they don’t have to think about state tax settings.

So your company’s In-N-Out reimbursement policy is a taxable benefit. But how do you tax a burger that's already in your belly? In payroll, this problem is solved with what’s called an “in-and-out.”

“I was disappointed to learn that I was paid the same as the guy checking receipts at Walmart.” He said in his annual self-review after getting a big, fat check.

Imputed pay is a type of non-cash benefit whose value is still taxable by the IRS. It could be life insurance, a domestic partner’s benefits, bills your employer paid for you, gifts. Answer: Your payroll person adds an “imaginary” dollar to your paycheck.  That’s imputed pay.

I’m talking about the small business where an employee is on their spouse’s insurance or a Marketplace plan and the company just reimburses them for all or part of the premium like a regular business expense. You're not supposed to do that.

If you’ve been trapped in your workplace unable to leave, eating Doritos from the vending machine for dinner and sleeping under your desk, should you be paid for that time?

Here's a rule of thumb: The best states to work in are some of the worst states to work with.

Before you start planning how you’ll spend that “free” paycheck before your finance department re-balances the budget for 2026 you need to know that your payroll provider is probably smart enough to anticipate this. There are two methods that payroll providers use to solve the 27-paycheck problem: Pro rata and pay as usual.

These days, it seems obvious that workers should be able to demand an accurate accounting for their time. But it wasn’t always that way. 

When someone is paid for a day they didn't work, it MUST be entered into payroll as some kind of Paid Time Off type. Otherwise, there's no way to pay it. Most of the uncommon leave types don't allow negative balances in payroll systems. So if your time off isn't allocated to another bucket, it can't get paid. The discrepancy could even block payroll and prevent everyone from getting paid.

Here are five examples of mundane breakdowns that I’ve seen lead to payroll errors:

Except that something didn’t add up. They didn’t even have employees for half that time, and one of the people they were assessing violations on wasn’t even in the state. 

When you’re the one who makes sure that everything is done by the book, there’s no one left to manage your exit correctly. That often means that you’re more likely than anyone to be underpaid or have your exit mishandled. 

Letters from government agencies can be real scary sometimes. Especially when they contain words like "Warrant" and penalties with commas in them. By all means, take these letters seriously. But don't let them scare you.

But what passes for “security” in these agencies is a cruel joke. It is no more realistic for you to expect me to tap Mr. or Ms. Business Owner on the shoulder and hand them the phone than it is for me to demand that you tap the governor on the shoulder and get him/her on the phone. 

Nearly everything that happens in the company goes through payroll. And the person managing it needs to have the skills of an accountant, IT, lawyer, insurance agent, and operations manager, all rolled into one.